[(dimethylamino)[(2-oxo-1,2-dihydropyridin-1-yl)oxy]methylidene]dimethylazanium; tetrafluoroboranuide

• ChemBase ID: 100173
• Molecular Formular: C10H16BF4N3O2
• Molecular Mass: 297.0575528
• Monoisotopic Mass: 297.12717005
• SMILES: n1(c(=O)cccc1)OC(=[N+](C)C)N(C)C.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.CN(C(=[N+](C)C)On1ccccc1=O)C
• InChI: InChI=1S/C10H16N3O2.BF4/c1-11(2)10(12(3)4)15-13-8-6-5-7-9(13)14;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1
• InChIKey: CZQGINAUZYECAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(dimethylamino)[(2-oxo-1,2-dihydropyridin-1-yl)oxy]methylidene]dimethylazanium; tetrafluoroboranuide
• IUPAC Traditional name: [(dimethylamino)[(2-oxopyridin-1-yl)oxy]methylidene]dimethylazanium tetrafluoroborate
• Synonyms: O-(1,2-Dihydro-2-oxo-1-pyridyl)-N,N,N′-N′-tetramethyluronium tetrafluoroborate; TPTU; O-(1,2-Dihydro-2-oxopyridin-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2-(2-Pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; N,N,N',N'-Tetramethyl-O-(2-oxo-1,2-dihydro-1-pyridyl)uroniumtetrafluoroborate; O-(2-Oxo-1(2H)pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate; O-(1,2-二氢-2-氧-1-吡啶)-N,N,N',N'-四甲基硫尿四氟硼酸; O-(1,2-二氢-2-氧代-1-吡啶基)-N,N,N′-N′-四甲基脲四氟硼酸盐; O-(2-氧代-1(2H)吡啶基)-N,N,N′,N′-四甲基脲四氟硼酸盐

Database IDs

• CAS Number: 125700-71-2
• MDL Number: MFCD00075475
• PubChem SID: 162086279; 24863208; 24862565
• PubChem CID: 2733204

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.860349
• LogD (pH = 7.4): -2.860349
• Log P: -2.860349
• Molar Refractivity: 70.8949 cm^3
• Polarizability: 22.007235 Å^3
• Polar Surface Area: 35.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140 °C (dec.)(lit.); 140°C; ca 140°C dec.

Safety Information

• Storage Warning: Irritant/Keep Cold/Light Sensitive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 37
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC); 97%; 98%
• Empirical Formula (Hill Notation): C10H16BF4N3O2

DETAILS

Sigma Aldrich - 365726

Packaging
1 g in glass bottle

Sigma Aldrich - 37347

Other Notes
Coupling reagent for peptide synthesis, especially suited for segment condensation with little racemization3
Packaging
5, 25 g in glass bottle
Application
Reagent for: Amidation1 Peptide Coupling2,3 Esterification of nucleosides to solid phase supports for oligonucleoside synthesis4

REFERENCES

• Low racemization peptide coupling agent: Tetrahedron Lett., 30, 1927 (1989). See Appendix 6.